Best Vacation Homes in Windsor
Cabin
- Parking
- Pet Friendly
- TV
Apartment
- 753 ft² Apartment
- Air Conditioner
- Parking
- Accessibility
Cottage
- Air Conditioner
- TV
- Balcony/Terrace
Cabin
- Parking
- Balcony/Terrace
- Security/Safety
Windsor Luxury Rentals
House
- Air Conditioner
- Security/Safety
- Bedding/Linens
House
- 2798 ft² House
- Air Conditioner
- Parking
- Balcony/Terrace
Villa
- Air Conditioner
- Parking
- View
Windsor Pet Friendly Vacation Rentals
Cottage
- Air Conditioner
- Parking
- Pet Friendly
Hotel
- 624 ft² Hotel
- Parking
- Pet Friendly
- Accessibility
Windsor Large Vacation Homes
House
- Air Conditioner
- Parking
- View
Why Choose Rent By Owner for your Windsor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windsor
How to Book Your Windsor Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Windsor Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:
- Highlands on Homestead -Tranquil rural property only minutes from town
- The Sun set Cottage 5min from Oamaru or Kakanui
- Little Sweetie in the Heart of Old Oamaru
- The Shepherd's Rest with alpaca, sheep & outdoor bath. Close to Oamaru.
- Historic Cottage in rural Oamaru with farm animals and outdoor baths
- Casa Nova House
- Exquisite Luxury Property with Stunning Views
- Cozy 2 Bedrooms Lavender Garden House at Oamaru, sweet as home!
- Peaceful cottage in private garden setting.
- Relax on Reservoir
2. Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
3. How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 154 in the Windsor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor.
Windsor Top Rated Vacation Rentals
Bed & Breakfast
- 301 ft² Bed & Breakfast
- Parking
- Pool
- Balcony/Terrace
